Patent GB-793796-A (GB)
Title: Substituted 1-aziridinyl quinones and a process for their preparation
IPC: C07D203/14
Filed: 1955-03-09
Abstract: The invention comprises substituted quinones and naphthoquinones of the general formul : <FORM:0793796/IV (b)/1> and <FORM:0793796/IV (b)/2> wherein X and Z represent alkoxy, alkanethioaralkoxy, aralkanethio, alkaryloxy, alkaryl, thio, araloxy, arylthio, dialkylaminoalkoxy or dialkylaminoalkanethio radicals, and including compounds where in the case that X or Z is an alkoxy, alkanethio, aryloxy or arylthio radical it may be further substituted by an alkoxy radical, in the case that X or Z is an alkanethio radical it may be substituted by a free hydroxyl radical, and in the case that X or Z is an alkoxy radical it may be substituted by an alkanethio radical and further including compounds where the radical Z is such as to form a symmetrical compound having two 1-aziridinyl naphthoquinone groups attached to a dithioalkane radical such as a 2-(1-aziridinyl)-3-(1,4)-naphthoquinolyl thioalkanethio radical, and <FORM:0793796/IV (b)/3> is a 1-aziridinyl radical in which R represents hydrogen or a C1-C2 alkyl radical, and the preparation thereof by reacting a halogen substituted 1-aziridinyl quinone or naphthoquinone represented by the above formul , except that X and Z represent halogen atoms, with an alkali metal compound of the required alcohol, thioalcohol, phenol or thiophenol.  The preferred compounds are those in which X and Z are alkoxy groups containing not more than 4 carbon atoms, or methoxyethoxy or ethoxyethoxy groups or dialkylaminoethoxy groups containing not more than 6 carbon atoms. The above process may be carried out in an inert solvent at low or high temperatures.  The alkali metal compounds used as reactants are preferably sodium and potassium compounds of aliphatic alcohols such as methanol, ethanol, n- and iso-propanol, n-, iso-, and t-butanol and higher normal and branched-chain primary, secondary and tertiary monohydric alcohols which may also be substituted by alkoxy or alkanethio groups; of phenols such as phenol itself, naphthol and alkyl substituted phenols including cresols and xylenols; of thiols such as methane-, ethane-, and propane-thiol as well as higher thiols of the aliphatic series including dodecyl- and hexadecyl-thiol; of aralkanethiols such as benzthiol; of thiophenols such as thiophenol itself and alkyl substituted thiophenols such as thiophenol itself and alkyl substituted thiophenols; and of mixed hydroxyl-thio compounds such as b -hydroxyethanethio and b  - hydroxypropanethiol. Suitable benzoquinone and naphthoquinone reactants are 3,6-dichloro (and dibromo)-2,5-di - (1 - aziridinyl) - 1,4 - benzoquinone, 3,6-dichloro - 2,5 - di - (2 - methyl - 1 - aziridinyl)-1,4 - benzoquinone, 3 - chloro - 2,5 - di - (1-aziridinyl) - 1,4 - benzoquinone, and 3 - chloro2 - (1 - aziridinyl) - 1,4 - naphthoquinone.  In the examples the following compounds are prepared: 3,6-dimethoxy-2,5-(1-aziridinyl)-1,4-benzoquinone and the corresponding 3,6-diethoxy-, 3,6-di-n-propoxy-, 3,6-di-n-butoxy-, 3,6 - di - (b  - methoxyethoxy) -, 3,6 - di - (b -ethoxyethoxy) -, 3,6 - di - (methanethio) -, 3,6-di-(ethanethio)-, 3,6-di-(benzenethio)-, 3,6-di-(4 - methoxybenzenethio) -, 3,6 - di - (benzylthio) -, 3,6 - di - (b  - diethylaminoethanethio)-, 3,6 - di - (b  - dimethylaminoethoxy) -, 3,6 - di-(o  - hydroxybutylmercapto) -, 3,6 - di - (b -methoxyethylmercapto) - and 3,6 - di - (b  - methylmercapto - ethoxy) - compounds; 3,6-diethoxy - and 3,6 - di - (ethanethio) - 2,5-di - (2 - methyl - 1 - aziridinyl) - 1,4 - benzoquinone; 3-ethoxy-, 3-phenoxy-, 3-methanethio-, 3-ethanethio-, 3-benzylthio-, and 3-o -hydroxybutylmercapto) - naphthoquinone - 1,4; and s,s1 - bis - [2 - (1 - aziridinyl) - 3 - (1,4)-naphthoquinonyl] - ethane - 1,2 - dithiol.  Specification 762,723 are referred to.